Thianthrene

Thianthrene
Thianthrene
Identifiers
CAS number 92-85-3 YesY
PubChem 7109
ChemSpider 6842 YesY
EC number 202-197-0
ChEMBL CHEMBL488176 N
Jmol-3D images Image 1
Properties[1]
Molecular formula C12H8S2
Molar mass 216.32 g mol−1
Melting point

151-155 °C, 424-428 K, 304-311 °F

Boiling point

364-366 °C, 637-639 K, 687-691 °F

 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Thianthrene is a sulfur-containing heterocyclic chemical compound. It is the sulfur analog of dibenzodioxin (commonly known as dioxin). Unlike dioxins, the shape of thianthrene is not planar. It is bent, with an angle of 128° between the two benzene rings.[2][3][4]

Thianthrene can be prepared by reacting disulfur dichloride with benzene in the presence of aluminium chloride.[5]

History

Thianthrene was first synthesized by John Stenhouse by dry distillation of benzenesulfonic acid sodium salt.[6] Thianthrene reacts with sulfuric acid forming a red product. R. Wizinger was the first to publish the structure of the colour giving cationic radical in 1929.[7] Although the structure was published several researchers used Thianthrene•+ for Electron paramagnetic resonance studies in the 1960s. Four different publications on the structure of Thianthrene•+ were published without knowledge of the other research.[8]

References

  1. ^ Thianthrene at Sigma-Aldrich
  2. ^ Hosoya, S. (1963). "Molecular shapes of thianthrene and related heterocyclic compounds". Acta Crystallographica 16 (4): 310–312. doi:10.1107/S0365110X63000797. 
  3. ^ Gallaher, K. L.; Bauer, S. H. (1975). "Structure and inversion potential of thianthren". Journal of the Chemical Society, Faraday Transactions 2 71: 1173–1182. doi:10.1039/F29757101173. 
  4. ^ Aroney, M. J.; Le Fèvre, R. J. W.; Saxby, J. D. (1965). "92. Molecular polarisability. The apparent conformations of thianthren and of three of its oxides as solutes in benzene". Journal of the Chemical Society (Resumed): 571–575. doi:10.1039/JR9650000571. 
  5. ^ US patent 3997560, "Process for the manufacture of thianthrene", issued 1976-12-14 .
  6. ^ Stenhouse, J. (1869). "Ueber die Producte der trockenen Destillation der sulfobenzolsauren Salze". Annalen der Chemie und Pharmacie 149 (2): 247–255. doi:10.1002/jlac.18691490216. 
  7. ^ W. Dilthey: Versammlungsberichte Bonner Chemische Gesellschaft, Angewandte Chemie, Volume 42, Issue 24, pp. 668–670, 15. June 1929; doi:10.1002/ange.19290422405.
  8. ^ Shine, Henry J. (1998-07). "EPR and the History of the Thianthrene Cation Radical". Foundations of modern EPR. ISBN 9789810232955. http://books.google.com/?id=1LdKSYIQtPYC&pg=PA202. 

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Look at other dictionaries:

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  • thianthrene — noun The tricyclic heterocycle consisting of two benzene rings fused to that of a dithiin ring …   Wiktionary

  • thianthrene — thi·an·threne …   English syllables

  • thianthrene — thīˈanˌthrēn noun ( s) Etymology: International Scientific Vocabulary thi + anthrene : a crystalline heterocyclic parent compound C12H8S2 that is regarded as anthracene in which the two middle methylidyne groups are replaced by sulfur atoms and… …   Useful english dictionary

  • Thianthren — Strukturformel Allgemeines Name Thianthren Andere Namen 9,10 …   Deutsch Wikipedia

  • heteranthrene — noun Any heterocycle consisting of two benzene rings fused to a 1,4 diheterabenzene in which the heteroatoms are the same e.g. thianthrene …   Wiktionary

  • Dibenzo-1,4-dioxin — See also: 1,4 Dioxin, Dioxins and dioxin like compounds, and Polychlorinated dibenzodioxins Dibenzo p dioxin …   Wikipedia

  • Mesulfen — Systematic (IUPAC) name 2,8 dimethylthianthrene Clinical data AHFS/Drugs.com …   Wikipedia

  • tiantrenas — statusas T sritis chemija apibrėžtis Heterociklinis junginys. formulė C₆H₄:S₂:C₆H₄ atitikmenys: angl. thianthrene rus. тиантрен …   Chemijos terminų aiškinamasis žodynas

  • тиантрен — tiantrenas statusas T sritis chemija apibrėžtis Heterociklinis junginys. formulė C₆H₄:S₂:C₆H₄ atitikmenys: angl. thianthrene rus. тиантрен …   Chemijos terminų aiškinamasis žodynas

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